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Sodium Carbonate → 3-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide

HRID 2193023
ノート
印刷プレビュー

反応式

HRID 2193023 の反応式
Br[C:2]1[CH:24]=[CH:23][C:5]2[C:6]([CH:20]([CH3:22])[CH3:21])=[N:7][C:8]3[C:9]([C:15]#[C:16][C:17]([NH2:19])=[O:18])=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd]Cl.CN(C=O)C>[CH:20]([C:6]1[C:5]2[CH:23]=[CH:24][C:2]([C:29]3[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=3)=[CH:3][C:4]=2[C:13]2[C:12](=[O:14])[NH:11][CH:10]=[C:9]([C:15]#[C:16][C:17]([NH2:19])=[O:18])[C:8]=2[N:7]=1)([CH3:21])[CH3:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 593756833-(9-Bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamideHCID 86761722dppp CH2Cl2

生成物 1

HCID 593753663-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

3-(9-bromo-6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl)prop-2-ynamide (57 mg, 0.15 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (62 mg, 0.30 mmol), and PdCl2(dppp-CH2Cl2 adduct (24 mg, 0.030 mmol) were added to a vial, followed by DMF (1.8 ml) and aqueous sodium carbonate (2M) (0.15 ml, 0.30 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 10 min, then heated in a microwave reactor at 100° C. for 30 min. The mixture was cooled, diluted with DMF, and filtered to remove salts. The solution was purified directly by preparative reverse phase HPLC eluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient, to afford 3-[6-isopropyl-9-(1-methyl-1H-pyrazol-4-yl)-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridin-4-yl]prop-2-ynamide. 1H NMR (500 MHz, DMSO-D6) δ 12.15 (br s, 1H), 10.15 (s, 1H), 8.46 (d, 1H), 8.34 (s, 1H), 8.01-7.98 (overlapping m, 3H), 7.89 (br s, 1H), 7.56 (br s, 1H), 4.08 (septet, 1H), 3.92 (s, 3H), 1.41 (d, 6H). LRMS (ESI) calc'd for (C22H19N5O2) [M+H]+, 386.2; found 386.1.

後処理

  1. customThe resulting suspension was purged with argon (subsurface bubbling) for 10 min
  2. temperatureThe mixture was cooled
  3. additiondiluted with DMF
  4. filtrationfiltered
  5. customto remove salts
  6. customThe solution was purified directly by preparative reverse phase HPLC
  7. washeluting with an acetonitrile/water (with 0.05% TFA as a modifier) gradient

出典と根拠

ORDレコード
ord-833670c25b884cabbb056b97224ad00d
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329722B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート